Portland, Maine is a historic seacoast town with a funky vibe, working waterfront, art galleries galore, and unique boutiques. The award winning restaurants serve everything from classic lobster rolls to exotic cuisine that is stylish and sophisticated, yet genuine and unpretentious. Experience the quintessential Maine Coast and urban sophistication, as well as lighthouses, lobsters, and surf crashing on the rocky shore. Vacationland!
The Small List
Best Hotels
Portland Regency Hotel & Spa – Situated in the heart of the “Old Port District”, the hotel is surrounded by a variety of specialty shops, galleries and restaurants. Many of which have been converted from the warehouses and commercial buildings that were original to the city’s maritime heritage. It was constructed in 1895 as the Maine National Guard Armory. The detailed Neo-Gothic Romanesque building was said to be one of the finest and best-equipped armories in New England. Also, it was a prominent feature in the Portland cityscape.
Inn By the Sea – Located about five miles south of Portland on the southern Maine coast, Cape Elizabeth is home to this oceanfront luxury resort hotel on a mile of sandy beach. Nestled on the beach, a beautiful place to get away from it all…just steps from the Atlantic Ocean.
Best Restaurants
Fore Street – Maine’s signature five star restaurant. The interior surrounds a unique brick and soapstone hearth with a wood-burning oven, grill and turnspit…beautiful, fragrant and visible from most tables.
Street & Co. – A Mediterranean, bistro style, all-seafood restaurant with a dynamic atmosphere and 20 years of experience. They are located in the Old Port district just blocks away from Portland’s working waterfront. Their chefs focus on serving the freshest seafood and the best ingredients available from local purveyors, fishermen and organic farmers. Al fresco dining is a highlight!
Best Bars
Gritty’s – Undeniably, the pioneer in Maine Craft Beer serving fresh ales and great food.
The North Point – This cozy wine and cocktail bar is a hot destination in Portland. Exposed brick walls and expert cocktail and wine pairings with meat, cheese, flatbreads and crêpes. Of course, the affordable price makes it a favorite “go-to” place.
Best Place to Stay in Casco Bay
Chebeague Island Inn – Built in the 1920’s, the Inn looks like a large home with classic beauty. And it is your home while you are there. Grab a bike from the Inn and take a cruise to the General Store. Afterwards, go to one of the many beaches. Chebeague (pron: shuh-Beeg) is one of Maine’s most beautiful islands. It is currently home to 400 year round residents, many whose families have been here for generations. There are two ferries that go to Chebeague Island: Casco Bay Lines and Chebeague Transportation Company.
Best Restaurant in Casco Bay
Chebeague Inn Restaurant – The restaurant at the Inn features seasonal, local ingredients from the island farm, the Chef’s garden out back and a lobsterman who fishes just off the coast and brings the kitchen lobsters daily. Obviously, a popular spot for boaters, guests and locals.
Something to See
The Portland Head Light – Cape Elizabeth is the home of the historic Portland Head Light. The lighthouse has a commanding setting at the southwest entrance to Portland harbor, and beautifully landscaped grounds. Situated along the spectacular shores of Fort Williams Park, this beloved head light was first lit on Jan. 10, 1791. Today, it continues to protect Portland and the adjacent area.